William Hale Thompson

William Hale "Big Bill" Thompson (14 May 1869-19 March 1944) was Mayor of Chicago from 3 November 1915 to 3 November 1923 (succeeding Carter Harrison, Jr. and preceding William Emmett Dever) and from 3 November 1927 to 3 November 1931 (succeeding Dever and preceding Anton Cermak). A member of the Republican Party, he was the last Republican to hold mayoral office in Chicago as of the 2010s, and he was known for his open alliance with Chicago Outfit boss Al Capone.

Biography
William Hale Thompson was born in Boston, Massachusetts in 1869, and his family moved to Chicago, Illinois when Thompson was nine days old. Instead of attending Yale University, he moved to Wyoming to become a cowboy and cattle owner, and he took up ranching in Texas and New Mexico. In 1892, he returned to Chicago to manage his father's estates after his death, and he was nicknamed "Big Bill" during his participation in athletic clubs.

In 1900, he was elected alderman for Chicago's 2nd Ward, and, in 1902, he became a member of the Cook County Board of Commissioners. In 1915, he was elected Mayor of Chicago as the Republican candidate, and he charged city drivers and inspectors $3 a month with the hope of funding a future presidential campaign. His opposition to US participation in World War I weakened his 1918 US Senate run, but he was re-elected in 1919 with the support of African-American voters. He looked towards drastically expanding Chicago, and he declined to run for re-election in 1923. However, he ran again in 1927 during citywide gang war, and Al Capone's Chicago Outfit threw grenades at polling places to disrupt voting, helping Thompson win re-election. However, his failure to clean up Chicago's reputation as the capital of organized crime and his xenophobia shown towards the Democratic Party politician Anton Cermak alienated Chicagoan voters, and Thompson's political career was ruined. He died in 1944.